Grand Master Award
The Grand Masters trophy will be awarded to the highest placing skippers over the age of 65 in the A, B and C Divisions at the Fleet 1 championships.
| Division | Year | Skipper |
| A | 2023 | Kurt Wiese |
| 2022 | Kurt Wiese | |
| 2021 | Kurt Wiese | |
| 2020 | Doug Rastello | |
| 2019 | Argyle Campbell | |
| 2018 | Argyle Campbell | |
| 2017 | Tucker Cheadle | |
| 2016 | Argyle Campbell | |
| 2015 | Argyle Campbell | |
| 2014 | Argyle Campbell | |
| 2013 | Bob Yates | |
| 2012 | Tom Schock | |
| 2011 | Tom Schock | |
| 2010 | Tom Schock | |
| 2009 | Bob Yates | |
| 2008 | Lee Sutherland | |
| 2007 | Terry Gloege | |
| 2006 | Jim Kerrigan | |
| 2005 | Bob Yates | |
| B | 2023 | Ed Kimball |
| 2022 | Greg Newman | |
| 2021 | Greg Newman | |
| 2020 | Jeff Gordon | |
| 2019 | Jay Swigart | |
| 2018 | Win Fuller | |
| 2017 | Pat Scruggs | |
| 2016 | Tom Corkett | |
| 2015 | Tom Corkett | |
| 2014 | Tom Corkett | |
| 2013 | Win Fuller | |
| 2012 | Richard Blatterman | |
| 2011 | Win Fuller | |
| 2010 | Bill Allen | |
| 2009 | Rolly Pulaski | |
| 2008 | Ted Munroe | |
| 2007 | Kathy Sangster | |
| 2006 | Richard Blatterman | |
| 2005 | Glyn Davies | |
| C | 2023 | Joyce Ibbetson |
| 2022 | None Awarded | |
| 2021 | None Awarded | |
| 2020 | Ed Watson | |
| 2019 | Win Fuller | |
| 2018 | Judy Weightman | |
| 2017 | Kathy Sangster | |
| 2016 | Rolly Pulaski | |
| 2015 | Dick Somers | |
| 2014 | Dick Somers |